


Looks Good on You

by evansrogerskitten



Category: Dean Winchester - Fandom, SPN, Supernatural
Genre: Cowboy AU, Dean in Wranglers (yes that's a warning), Dirty Talk, F/M, Oral Sex, blowjob, cursing, implied sequel, roadhead
Language: English
Status: In-Progress
Published: 2018-07-09
Updated: 2018-09-06
Packaged: 2019-06-07 14:35:17
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 4,853
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15221303
Author URL: https://archiveofourown.org/users/evansrogerskitten/pseuds/evansrogerskitten
Summary: After helping out with some chores Cowboy!Dean gets a special thank you on the ride home.





	1. Chapter 1

**Author's Note:**

> This is for Jensen x Hats Challenge, Dean's hat had to play a significant role. Also for Kink BINGO: Roadhead square.

“ _Uhh_ ,” I grunted as I swung a bale of hay onto the bed of the truck, heaving the forty pounds with all my strength. I pushed the green straw into line with the other blocks. The late afternoon sun was starting to drift down as a dove flew over head, settling in a cottonwood tree with a soft coo.

“Watch out,” Dean warned as he lifted the last two heavy bales. I brushed dirt and bits of hay off my worn jeans before sliding my work gloves off. The bed of the truck slammed shut and Dean grinned at me over the rows of hay.

“All in a day’s work, righ’ darlin’?” he drawled.

I smiled and matched his southern accent with my own, “Thanks for helpin’ me get these out.” I tugged on the rope ties to make sure they were tight enough. I glanced back at the old red barn where I’d been storing the surplus. “Been so busy with the new foals, didn’ know when I’d get out here.”

“Always gonna help my girl,” Dean winked. I swiped my hands across my thighs one last time and climbed up into Dean’s black Chevy pickup. He closed the barn door and sauntered up to the truck.

Dean Winchester had all the girls in town swooning, regardless if he was spoken for. The country boy was known for his hard work and integrity, coming from a family well known around these parts. He was a good man, and I was lucky to know him, even luckier to be his girl. I knew he was a catch; all muscle and charm and sin that made my heart skip as I watched him saunter towards the truck. His faded jeans clung to his thick thigh muscles as he walked across the dirt driveway, his bow legged stance just as appealing as when he was riding bulls at the annual rodeo or holding me in place on his bed late at night. His plaid shirt was rolled up to mid arm, dust marks on the muscles of his forearms that his gloves hadn’t covered. He knocked the dirt and straw off his scuffed work boots on the truck’s running board before climbing in.

“Let’s go Baby.” Dean patted the dash of his precious truck. He switched the radio to play a country tune as the diesel engine rumbled beneath us. His hand paused on the shift lever, brows furrowed as he searched the cab.

“Hold up.” He hopped out of the truck and jogged back to the fence post where he’d hung his Stetson during our strenuous chores.

“Cowboy can’ forget his hat,” I teased as he returned to the seat next to me.

Dean smirked and set his wide-brimmed hat on the dash. “Ya know ya love me in my hat.”

“Looks real good on you,” I winked.

We listened to the radio in comfortable silence, the gradual speed of the truck cooling the hot summer air as it blew in the windows. The sweet scent of the dry hay wafted in over our shoulders through the small window at the back of the cab. I looked over at the handsome man next to me.

“You gonna take me out tonight, Dean?”

Dean lips turned up in a soft smile, his left wrist slung across the wheel as his right hand took mine and tugged me closer. He slung his right arm around my shoulders as he looked ahead. “Anywhere you want, honey.”

“There’s supposed to be dancin’ at Miss Harvelle’s,” I suggested casually, even though I really wanted to go. “Jess told me Sam asked her to go with him.”

“Well, only if ya get all dolled up for me,” Dean bargained, “wear that green dress I love.”

I smirked, reaching up to pull a short pale green piece of straw from his hair, lightened to sandy blonde from working out in the sun every day.

“I can do that, cowboy,” I breathed before placing a kiss on his neck. Dean groaned as I repeated the kiss just under his ear. The back of his neck was warm, the exertion of hauling the hay earlier flushing his skin. I kissed each sun-coaxed freckle until Dean adjusted in his seat. Suddenly I had another idea.

I slipped under his arm and scooched my knees back on the bucket seat, far enough that I could lay on my stomach. Dean looked down in surprise as I rested on my elbows on the seat and my hands unlatched his brass belt buckle.

“Whatcha doin’?”

I shrugged, pushing his belt aside and pulling the zipper of his Wranglers down. “Jus’ a lil preview of tonight’s after party.”

Dean groaned as he lifted his hips and widened his thighs so I could have better access. I moved the cotton seam of his underwear aside, biting my lip as I released his cock. It hardened with my strokes; my small hand quickly stretched around his girth. He’d tucked his lower lip underneath his top teeth, trying desperately to pay attention to the road but also to watch me.

“Oh god,” Dean groaned as I licked a circle around the head. His skin was salty and tangy under my tongue, and I wiggled my hips into the seat as I got comfortable, the tips of my boots resting half out of the passenger side window. I teased him a few times, suckling and licking the drops of pre cum as they appeared, teasing the swollen nerves on the underside. Dean groaned loudly over the music as I took him in my mouth, bobbing up and down slowly. His hips started to rise up to meet my mouth as he gripped the steering wheel hard, desperately trying to keep his eyes on the road. Dean’s hand came down and pulled the band out of my hair, his fingers nestling in the loose strands.

“Feels...god, so... _so good_ ,” Dean stuttered. The truck swerved at my next long suck and I lifted my head with a giggle. I loved knowing I could do this to him in a matter of minutes no matter where we were.

“Don’t go killin’ us out here,” I smiled up at him. I went back to my task, loving the rewarding noises above me, the clutching at my hair, the pulsing vein under my tongue. Dean’s hand left my hair to smack on the steering wheel as I took him deep again.

“Christ. Yah keep doin’ that I’m gonna come,” Dean’s voice was wrecked and gruff as he shifted in his seat with another loud groan. The vehicle swayed across the dirt road as he smacked the back of his head on the headrest. “So good, darlin’.”

I moaned, happy as Dean grew even harder as he neared orgasm.

“Awww hell,” Dean suddenly announced, his hips stilling and his warm hand resting on my neck to keep me still.

“What?”

“Sheriff,” he replied, looking in the rearview. I pulled my legs down and started to sit up but Dean shook his head. “Just stay down, they’ll see ya.” He grabbed his hat off the dash and placed it on my head, as if he was camouflaging the part of me that was causing the most trouble.

“Well, if I’m here,” I replied under the shade of the hat. Dean’s cock slid in and out of my mouth as I opened my jaw wide, really taking him in, loving the desperate moans that he was trying to stifle as he did his best to control the truck. This was dangerous, and I knew we’d both be in serious trouble if the police pulled him over, even worse if it was his Uncle Bobby on patrol. But I wasn’t gonna stop until I drank him dry.

“ _Fuck_ , honey I...gonna come...” Dean cursed under his breath. He cleared his throat, raising a shaky hand to salute the sheriff as they passed us. But I didn’t care if they were gone or not. Dean was rock hard and hot in my mouth, moments away from exploding. I smiled at the little cursing whines he made as his hips thrusted up to meet my mouth; once, twice, and then he was coming with a low groan, hot and salty on my tongue. I lapped it all up, swallowing and sucking him clean until he was too sensitive for even kitten licks.

“Hot damn,” Dean’s cheeks were red, his neck splotchy in spots, and his forehead sweaty. I sat up and redressed him, and then pressed his hat down on my head a little off center, prompting a low groan of approval as I licked my lips. Dean swept the back of one hand across his forehead and sighed, glancing back and forth between me and the road.

“Damn, woman you are amazing,” he smiled. “Look so good in my hat too. C’mere.”

I scooted closer and kissed him, a soft press of my lips on his, the truck drifting again. “You love me in your hat,” I grinned, settling back into my seat and taking a deep breath. “May jus’ have to wear it tonight.”

“With your green dress?” Dean asked hopefully.

“Maybe. Or with nothin’ on,” I giggled.

Dean groaned, shaking his head with an eager smile as we drove the last half mile to my house. I watched my fields pass by, the open window letting in the warm breeze as I noted which horses needed to be brought in before suppertime. I turned my head back to the driver and found him watching me affectionately.

“How about this, darlin’? You wear nothin’ under that green dress tonight, and I promise when we get home I’ll wear nothin’ but that hat for ya.”

I straightened the brim of his hat and smiled. “Ya got yourself a deal, cowboy.”

  


  
+++++

Should I write more of these two? I kind of want a sequel of them dancing at Miss Harvelle’s and Jess and Sam being there all midwestern and it being adorable. Yes? I reckon so!  



	2. Chapter 2

**Summary for the Chapter:**

> Cowboy Dean makes good on his promise.

**Notes for the Chapter:**

> This is for Kink Bingo: Free Square and Genre Bingo: Chick Flick Moment
> 
> Cowboy!Dean x Reader, featuring Sam x Jess, Bobby x Ellen

“Alright honey, be back in thirty.” Dean wrapped his arms around me from behind, placing a kiss on my cheek and then one under my ear. “Green dress, alright?”

I laughed, playfully knocking my hip against his as I collected our dirty supper dishes. “You sure are in love with that dress.”

“Nah, just in love with the girl that looks so good in it.” With a wink he was out the door, and I was still smiling as his truck rumbled out of the driveway and down the road towards his place.

I took a quick shower, using the flowery body wash that made me feel feminine in contrast to a hard working ranch owner that’d aided the birth a calf, farmed three acres, and with Dean’s help lifted and stored 500 pounds of hay all in the day’s work. After setting my hair in velcro rollers like my mama taught me years before, I applied some powder and mascara, and just a dash of the red lipstick I kept for nights out. I went to my armoire to select a bra and panty set to wear under my dress. But I smirked when I heard Dean’s truck door shut outside the open bedroom window. Okay, no panties.

A high pitched whistle of appreciation greeted me as I descended the stairs in my emerald green dress and brown wingtip boots, the special occasion leather ones with the delicate white lilies embroidered on the sides. My breath caught in my throat when I took in the tall drink of water standing in my living room.

Dean was a daydream, a cowgirl’s fantasy. His sandy blonde hair was still a little damp but I could see he’d tried to style the longer pieces on top before just giving up and brushing it to the side. His navy long sleeve snap shirt was tucked into his nice Wranglers, his usual buckle had been polished and shone where it accentuated his waist. The denim was just tight enough, not giving too much away, but with enough flex in the cotton to show the curves of those bowed muscles and perfect ass. As he shifted to step towards me, I watched his thighs tighten under the dark denim and immediately wanted those hips to hold me down. His work boots had been switched out for his cleaner black ones that he didn’t like as well, but he knew I’d appreciate. He’d put on the cologne I’d picked out for him at Christmas, swathing me in a spicy musk that made me want to prove to him right then and there I was pantyless. Holy lord, what a man.

“My, my,” he grinned as he stepped forward, his clean white Stetson held reverently in front of his belt buckle as he looked me up and down. His eyes matched the color of my dress almost perfectly. “Honey, you look beautiful.”

“You’re not too bad yourself,” I replied, leaning up on my toes as his lips brushed against mine. Dean scratched the back of his neck, blush appearing on his cheeks like it always did when I told him how handsome he was.“You look so good in blue, baby.”

“Nah. You’re too sweet,” Dean kissed my cheek. I took a moment to revel in what a good man he was. Dean had inherited his parents’ ranch, successfully raising cattle rather than farm like his daddy before him. He’d won rodeo contests worth thousands, and was an absolute genius when it came to fixing anything mechanical. He would help old ladies across the street and bring me wild flowers for no reason. The man didn’t know how wonderful he really was.

I led the way out of the front door as Dean held it open, slowing by the truck door before he opened it for me. He held out his hand to help me climb in. As soon as I sat down Dean’s hand was on my smooth calf, running up to meet my knee. He arched an eyebrow with a mischievous silent question.

“Hey now, you promised me somethin’ too, remember?” I grinned. “I’m not missin’ that for the world.”

“Oh really?”

“Yeah, been thinkin’ about it for hours.”

Dean laughed. “You know my hat looks better on you.”

“It does,” I teased as I took it from him and set it in my lap.

Dean crossed in front of the Chevy and pulled the door open, climbing into his own seat. As he twisted the key in the ignition he looked over and winked. “I think we’re gonna have a good night.”

We left my house behind, the early evening setting in as the west sky faded into layers of tangerine and coral. Dean took my hand, his fingers sliding between mine as Kane Brown crooned on the radio. The breeze was cool, a welcome change to the ninety degree afternoon. The dark fields we passed were waking with wildlife emerging for an evening of their own.

“Looks like the whole damn town is here,” Dean chuckled as we reached the full parking lot of the most popular bar in the whole county. “Sam better have picked a table for us.”

I took his hand as he helped me out of the truck. Like a gentleman he placed his hand on my lower back and led me into the loud bar.

Harvelle’s Saloon was packed with folks from as far as three towns over. There was a live band playing and a few couples already dancing a do-si-do on the hardwood dance floor. We paused in the doorway and scanned the room, gaining the attention of the already buzzed patrons.

“There’s Sam.” Dean nodded towards a table on the left side. He took my hand and we weaved through groups of people collected by the bar. Business owners and farmhands alike greeted us, patting Dean on the back of the shoulder and tipping their hats to me. A few women fluttered their lashes in greeting to Dean, their eyes lowering when they noticed I was with him.

“Hey y’all,” Dean greeted Sam and his girl, Jess. Sam grinned, shaking his brother’s hand before tipping the lip of his black hat to me. Jess embraced me, her yellow dress dotted with little red and blue flowers. We’d been friends for years, and I’d set up the young blonde teacher with Dean’s brother six months before.

“Beer?” Sam asked as he started to pour glasses from the pitcher on the table. We accepted and sat around the table, chatting while the band played songs that we’d listened to our whole lives growing up in the country. As the band took a break and the music faded, the room hummed with loud talking and drunk laughter.

“So y’all, uh...there’s somethin’ Jess and I mean to talk to you about,” Sam looked over at Jess with a wide grin.

My instincts must’ve known by the look on both their faces to stray to Jess’ left hand which was resting on top of Sam’s. A gold band with a small round diamond adorned her ring finger. Dean noticed at the same time I did and we both looked up with wide eyes.

“We’re getting married!” Jess squealed, holding out her hand so we could see the ring better.

“Congratulations!” Dean grinned after a few seconds of surprise, leaping out of his chair to hug his brother and then Jess. “Found yourself a great gal, Sam. We’re real happy for ya, aren’t we sweetheart?”

“Of course!” I nodded, still a little stunned as I pushed my chair back so I could stand and hug my friends. “Six months, my my, you two move fast!”

Jess shrugged, tipping up on her toes to kiss her fiance. “When ya know, ya know. Right Sam?”

“Right, baby.” Sam drawled, grinning wide as he teased her. “Figure it’s time to make an honest woman of her.”

Jess blushed and smacked him playfully on the chest before kissing him again.

“Well I think this calls for whiskey,” Dean grinned, looking around for a waitress. I sat back in my chair next to him, my left hand finding his right and squeezing.

“Who called for what whiskey?” Dean and Sam’s Uncle Bobby appeared in front of us.

“Hey Uncle Bobby,” Sam smiled. “We were just telling these two that we’re...Jess and me, we’re gonna get married.”

Bobby grinned wide, slapping his thigh and cheering out loud, clearly a little drunk himself. “Woohoo! One of my boys gettin’ married?” The stocky man looked around and called out. “Ellen! Ellen! Where are you, woman? C’mere!”

Ellen, Bobby’s wife and co-owner of the saloon, appeared. “What’re ya hollerin’ about?”

“Sam and Jess here say they’re gettin’ married,” Bobby grinned.

Ellen’s face lit up with a happy smile. “Well then whiskeys all around! That’s wonderful news.”

After a round of drinks and congratulations, the band started up again. Dean stood, straightening his hat before offering his hand to me.

“Wanna dance, sweetheart?”

I set my beer down and nodded, taking his hand as I stood. “Always wanna dance with you, cowboy.”

We’d danced those patterns a thousand times in our lives, learning them as kids and perfecting them as adults. But Dean and I fell into place with each other instantly, laughing through a quick line dance or smiling at each other as he held me close during a waltz. I was glad to follow his lead, even when he was spinning me around as quick as his boot could stomp on the floor in time next to mine. I loved being there with him, my skirt twirling around my knees as he held my waist tight, out of breath at the end of a swing dance that had us both grinning like two idiots.

Eventually we fell back into our chairs, ordering another round of whiskey as we watched Sam attempt to teach Jess how to Two Step again. It was a good night, one of our best. And we hadn’t even made it home yet.

After wishing Sam and Jess a good night, Dean helped me into the truck and we headed to his place. I was tempted to repeat my oral performance from earlier in the day but the Chevy raced us up to the house in no time. We were barely out of the truck and to the screen door before we were kissing, Dean walking backwards with his arms around me as we stumbled into his two-story farmhouse. Our laughter was hoarse from the night’s drinks and day long desire as I clung tightly to him.

“No, keep it on,” I shook my head as Dean tossed his hat on the ancient oak dining room table. “You owe me another dance, cowboy.”

Dean chuckled as I grabbed the hat and stuck it on his head again. “Dance? I didn’t say anything about any dance, darlin’.”

“Hmmm, we’ll see,” I replied before stepping out of his arms. “Whoever makes it upstairs last, gotta strip first!”

“Awwww that’s not fair,” Dean groaned behind me as I half crawled up the hardwood stairs in a fit of giggles. The master bedroom door was open and I laughed as I fell backwards onto the bed. A few seconds later Dean appeared in the doorway.

“All I said was I’d wear my hat while we were makin’ love, sweetheart. No dancin’.”

I giggled as I twisted to lay on my stomach. “Strip, cowboy.”

Dean sighed hesitantly before shaking his head and giving in. With each snap of his shirt buttons the blush moved from his cheeks to his ears, his neck to his chest. I squealed when he tossed his shirt and then his undershirt at me. I couldn’t help but giggle as he hopped around shirtless on one foot and then the other to pull his boots off. He was equally adorable and the hottest man I’d ever seen. I wasn’t ashamed of the low moan in my throat as he pushed the Wranglers down, the muscles in his thick thighs shifting as he kicked the pants off. With each shedded layer my bare pussy got wetter, until the man I love, the perfect cowboy, was standing in front of me in just nothing but his white Stetson hat.

“Wow,” I breathed, looking him up and down. Each inch of freckled skin shone under the moonlight that was streaming through the window. My mouth watered as I relearned every muscle and tan line, my tongue lazily tracing my lip as I watched his cock harden under my gaze.

“Jeez darlin,” Dean blushed even redder, taking his hat off as if to cover himself, “I’m gonna get dressed if you’re gonna stare at me like that.”

“No!” I quickly jumped off the bed and walked towards him. My hands grazed down the freckled muscles of his shoulders, his arms, his tight abs, his waist- strong muscles worked hard in the sun every day. I craved being under all of that power.

Dean hissed as my hand wrapped around his cock, throbbing to its full weight in my palm. “You’re still dressed,” he reminded me.

“Hmmmm,” I nodded before leaning in and kissing him. As my mouth opened to his, Dean’s hands moved up my thighs and under the green dress.

“Fuck yeah,” he groaned as his hands cupped my bare ass, “all night I was thinkin’ how I couldn’t wait to touch you.”

“You asked me to forget the panties.” I moaned as he grasped my waist and thrusted his hips against mine. “I did, just for you.”

“Good lord, I love you so much, woman.”

Dean stripped me of my dress and bra, my boots kicked across the floor with a loud thunk. Naked we fell back on the bed, Dean’s hat falling to the end of the mattress as he moved between my legs.

“Been waitin’ for this all day,” he muttered before his tongue swept through my folds. I moaned, probably loud enough to wake the animals in the barn half a mile away. My fingers ran through his hair as his tongue circled my clit, my legs trembling on either side of his shoulders. He hummed against me as his calloused fingers slid inside, rough as they crossed the spot that made me stutter his name.

“De-annnn!”

“Christ,” Dean groaned as his plush lips sucked on my folds and then my inner thighs. He pushed himself up on his hands and knees and crawled over me. I could taste myself on his tongue and I moaned underneath him.

“Please,” I whispered, wrapping my legs around his waist, “need you.”

Dean chuckled, reaching to the end of the bed and grabbing his hat. He plopped the white canvas on his head and winked. “Promise to fuck ya like a real cowboy does.”

I moaned his name as he slid into me, pushing the hat back so it would give my lips better access to his throat. Dean groaned in my ear, thrusting into me harder and faster as we chased that blissful line. “Feel so good...oh sweetheart, fuck,” Dean stuttered.

I held onto his shoulders tight as Dean fulfilled his promise. We traded kisses with each deep thrust and my eyes rolled back in my head as he nailed my G-Spot again and again. My orgasm edged closer and closer, and Dean groaned as I clenched around his cock.

After a few minutes of being so deliciously close I pressed his shoulder back. “I wanna...on top.” Dean gulped, nodding as he hurried to flip over. I straddled him, moaning as I sank down over him again. I grabbed the forgotten hat and stuck it on my head, smirking at Dean as his grip on my hips tightened.

Dean groaned. “Looks so fuckin’ good on you. Come on, ride ‘em cowgirl.”

I rolled my hips, moving back and forth over him like I’d ride a stallion, the pressure in my core building until Dean was thrusting up to meet me. The whiskey, the bet, the pleasure, and the damn hat; I was over the edge before Dean could stroke my clit twice. He followed me, his eyes scrunching closed tight as he groaned my name over and over until I was full of his seed and we were both satisfied.

Panting I fell onto the bed beside him, the hat flopping onto the ground. Even though we were flushed and sweaty he wrapped his arm around me, our breathing steadying as we revelled in the dissipating bliss. Shadows from the old willows outside danced across the room, the bedroom quiet as we listened to each other breathe. Dean’s farm would wake in a few hours, as would mine. But for now, there was nothing in the world better than laying in bed with my cowboy.

“I saw ya, ya know, when Jess showed us her ring.” Dean tightened his arm around me to set a kiss on the top of my head.

“Hmmm?” I asked, my eyes closed as I listened to the symphony of his heartbeat and the chirping crickets outside.

“You were surprised,” he continued.

“Well yeah, they’ve only been datin’ six months.” I shrugged. “I’m very happy for them though.”

“Yeah,” Dean nodded. A dozen breaths passed before he spoke again. “Whatya think about somethin’... somethin’ like that?”

“A ring?” I asked.

Dean chuckled. “Well, sure. But, whatya think, you know, about a marriage? Like you and me?”

I leaned up on one elbow, as Dean tilted his head and looked at me. He brushed my tousled hair behind my ears, a small sweet smile on his lips as he waited for me to respond.

“Ya mean that?” I asked. “We never talked about gettin’ married, not seriously really.”

“Yeah. I wanna have a life with you.” He smiled and my heart did a little do-si-do of its own. “I wanna have you by my side runnin’ this place, maybe have a bunch of young ‘uns to drive us crazy. We can get old and sit in rockin’ chairs on the porch.”

I giggled, picturing that perfect dream that I now knew we both shared. “Are you proposing to me in bed in the middle of the night, cowboy?” I teased, my heart thumping like a wild bunny trapped under a wolf run.

“Nah,” Dean smiled as he rolled me down onto the bed beneath him. His hips settled between my legs and he kissed me, both of us breathless when he pulled away. “Just wanted to find out if you were the marryin’ kind.”

“Hmmmm, lemme think. I do love cowboys.” I teased. “You gonna keep strippin’ for me if I marry you?”

“Your turn next, sweetheart,” Dean smirked, my laugh of surprise silenced as he kissed me again.

The Stetson laid on the floor the rest of the night. But that was okay. We didn’t need it for round two anyway.

 

**⋘ ──── ∗ ⋅◈⋅ ∗ ──── ⋙**

**Please let me know if you enjoyed this! Kudos and comments are my fuel!**

**Author's Note:**

> Do not copy and paste my writing anywhere without my consent. This work is property of evansrogerskitten. ALL RIGHTS RESERVED. These works contain material protected under International and Federal Copyright Laws and Treaties. Any unauthorized reprint or use of this material is prohibited. No part of these works may be reproduced in any form or by any means, electronic or mechanical, including photocopying, recording, or by any information storage and retrieval system without express written permission from the author / publisher. An electronic reference link to the original posted work may be provided for purposes of promotion or assistance of publication by the readers discretion, if proper credits are given to the author in the re-post.


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